Three contenders vying to be Portland’s next mayor pick spots in the city that reveal the souls of their campaigns.

THISMAY, PORTLANDVOTERS will begin the selection of their next commander-in-chief, prime minister, head civic cheerleader, most prominent human dartboard, and lead political cat-wrangler—a fair, if incomplete, description of the mayor’s job here. Each of the three major candidates pursuing the city’s top post embodies a slice of Portland’s modern-day persona. Eileen Brady marries green and business interests. Ex-city commissioner Charlie Hales points to his experience with mass transit and progressive planning. State Rep. Jefferson Smith wants to mobilize youthful activists in the name of social equity. Together these three would form a perfect super-cyborg of Portland liberalism. Separately, telling their rhetoric apart can be a challenge.

Given the 23 candidates—almost all also-rans—crowding May’s mayoral ballot, and early polls showing none of the three leading hopefuls close to the 50 percent needed to win outright at the primary stage, a November runoff is considered likely. As one well-seasoned local wag puts it, “Right now, ‘undecided’ is running away with this thing.” Yet barring a wildly unforeseen development, one of these three people will be Portland’s next mayor.

So we offered each candidate a chance to set him or herself apart, inviting each to pick a specific place in Portland that captures their vision of the city.

The Southwest Community Center

“Should we start with the clothes on, or the clothes off?” No, it’s not that kind of encounter with a Portland politician. Charlie Hales just wants to show off the pool in this gleaming Portland Parks facility. Soon, he’s in the water up to his collarbone.

Zenger Farm, Southeast Portland

“Here, pretty. Hey, girlfriend!” Eileen Brady shakes chicken feed in her palm like a craps player rattling dice. Rain hammers down on the plastic roof of the chicken coop at this 16-acre complex of urban crops and wetlands. A russet colored bird resists her entreaties.

David Douglas High School, Southeast Portland

“Over 3,000 kids go here, and something like 80 percent are on free or reduced lunches,” says Jefferson Smith, standing before David Douglas High School’s leaping Scotsman mascot. “They speak 70 languages. This school, in some ways, is the gravitational center of the outer east side.”

Why Here?

“To me, this place symbolizes Portland’s willingness to pursue the common good. You can do the big, bold thing here.”

On a weekend afternoon, the community center at Gabriel Park is mobbed with kids and families, but there’s a vacant lap lane for the man who claims a large share of credit for building the place.

The pool is one result of a $58.8 million bond measure Charlie Hales proposed and fought for in 1994, when he was a first-term councilman running a budget-squeezed parks bureau. In Hales’s telling, the bond, which passed with more than 55,000 votes to spare, provides a small but telling profile in political courage: “I’m willing to stick my neck out.” In a larger sense, Hales’s campaign for mayor, a decade after he left City Council, rests on his argument that he is the one candidate who knows how to get stuff done.

In his days on city council, Hales quickly developed an appetite for the grand (and lasting) gesture. He pushed through the nation’s first modern streetcar, supported light rail, and oversaw bond-funded renovations of more than 100 parks. Even his minor projects showed a physical bent, like the briefly controversial Chinese bronze elephant statue he helped install on the North Park Blocks. When he left the council, it was for a private-sector job developing streetcars and light-rail lines.

Political observers say the 56-year-old is attempting what might be called a “Kitzhaber”: positioning himself as the race’s lone grown-up, the veteran who now wishes only to serve. Hales himself says,

“I don’t need to worry about my political career or my next elected job, because I won’t have one. I’m not on the political ladder anymore. This is it.”

“This place is a statement about the power of local people to take destiny into their own hands.”

After 15 minutes at Zenger Farm, the mayoral race’s current frontrunner wears a splotch of mud on the right knee of her jeans like a badge of earthy honor. The chicken-coop scene suggests nearly irresistible political metaphors. But suffice it to say that Eileen Brady, a 50-year-old rookie candidate, is likewise trying to charm voters, with an appeal based on the green values and public-minded, entrepreneurial spirit she finds at Zenger.

The farm occupies city-owned land but is run by an education-oriented nonprofit. Brady sat on Zenger’s board as it blossomed in the mid-’00s, playing a role in key hires and important grants. “When I first got involved, Zenger had no greenhouse, no farmhouse, and maybe 100 kids a year for educational events,” she says. “Now the programs serve over 5,000 kids a year.”

Brady’s campaign is attempting a similar barn raising, built on the foundation of the part she and husband Brian Rohter played in creating the beloved New Seasons grocery chain, backed by a hefty war chest. (The exact nature of her former role at New Seasons is a matter of some dispute.)

Brady uses the word “entrepreneurial” like a mantra. Her definition of the concept is broad, including public-private partnerships like Zenger, high-tech start-ups, and more traditional businesses. Brady puts great emphasis on straightening the “bureaucratic maze” faced by new businesses and curbing city fees. As to the latter, she cites potential reductions in cutting costs for start-ups in neighborhoods that need economic boosts.

“I want a livable city, but we have to have jobs. Sustainability involves economics and equity, as well as the environment.”

“Too often, we forget the width and breadth of the city. If we don’t make Portland a better place for more people, there won’t be too many more seasons of Portlandia.”

In a parking lot next to David Douglas on a winter Sunday, Jefferson Smith carries himself—at 6’4”, there’s a lot of him—with somber focus. The lot fronts a diverse and poverty-plagued school at Portland’s fast-growing eastern edge, the area Smith represents in the state House, and the unlikely staging ground for his battle to capture the city’s top political job.

Alone among the major candidates, Smith is a Portland native, and finds himself very much at home in intricate discussions of how the city works. When he really gets going, one sentence barely escapes before the next begins. Today, he’s in a lower gear—perhaps because the legislature’s February session has him working in Salem and running for mayor at the same time—but he still manages to weave tight-knit analyses of seemingly disparate elements of the city. For example, he sees the outer east side’s zoning for high-density housing, plus its relative lack of basic amenities like parks and paved streets, as part of a potent recipe for social change when combined with two decades of urban renewal in inner Northeast.

“That’s meant 10,000 low-income and minority folks moving from Northeast to the outer east side over the last 10 years,” he says. “What happened didn’t just happen. It was done, and often without anyone considering all the ramifications.” In Smith’s outlook, comparable stories could be told about many places in Portland, and demand a holistic vision.

“It takes an ethic and a discipline of seeing the whole picture.”

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The Pitch

“Of the candidates, I’m the one who has devoted a whole career to cities,” Hales says once he’s toweled off. “That’s been my focal point, whether in government or not: great cities in general, and ours in particular.”

When asked what voters don’t yet appreciate about her political approach, Brady sounds like the former HR director she is. “I’m a whole-systems thinker,” she says, “and that’s a significant value-add for the position.”

Smith promises to knock over the apple cart of local politics. “We don’t need to simply make the status-quo trains run on time,” he says. “The conversation needs to change if we’re going to build the city we want.”

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The Money

Given his emphasis on “place,” it’s no surprise that Hales’s fundraising relies largely on donations from developers, rail builders, and prominent real estate figures.

Brady has raised and spent much more than her rivals. Large donors include New Seasons cofounder Stan Amy, business execs, and members of the feminist organization Emily’s List.

Despite being banned from fundraising during the legislative session, Smith stockpiled scores of small-to-medium gifts at the end of January, keeping pace with Hales.

The Outlook

“There was no obvious funding for the streetcar or, for that matter, Pioneer Courthouse Square.”

If Hales becomes mayor, what’s the next “big, bold thing”? “We’ll find it,” he says—and how to pay for it. His own possibilities include transforming a defunct rail line along the Columbia into a cycling path to Astoria, and an idea seldom discussed since his days in City Hall: burying the east-bank freeway(That project was once penciled out at as much as $5.8 billion in 2003 dollars). Hales also cites unpaved roads, the many “five-acre blackberry patches” that could become East Portland parks, and making every neighborhood “a complete community” through classically Portland planning and development.

Hales scored a political coup by landing the endorsement of Vera Katz, the enduringly popular ex-mayor under whom he served. Otherwise, his campaign, so far, has a low-key feel. Hales shows up at the pool solo (his two chief rivals are escorted to their photo shoots by a campaign staffer), shortly after finishing the annual Worst Day of the Year bike ride, and leaves for a small coffee date with potential supporters.

Hales’s style leaves him open to criticisms that he’s fighting the last war. The build-it-and-they-will-come approach of the ’90s and early ’00s—when Portland developed huge chunks of the central city around the rail and streetcar projects Hales supported—may not fit the tight budgets and ever-more-complex economic and social issues of the ’10s.

In his council days, Hales could be sprightly, combative, and rarely shy about seeming the smartest guy in the room. These days, he exudes a more mellow energy: the wise uncle who’s seen a few things, but wants to see a few more. In a race that might, in the end, last more than a year start-to-finish, knowing a few local political war stories by heart could come in handy. Hales obviously thinks so.

“There’s no learning curve for this job. You become mayor right away when you’re sworn in.”

“I’m new to the political scene, and I don’t know how to talk in sound bites.”

The specifics of Brady’s policy proposals—and she can wonk with the best of them—seem to matter less, for now, than her larger message: that she could unleash Portland’s ambitions to be simultaneously sustainable, lively, and prosperous. And despite her yen for PowerPoint-speak, Brady is the candidate closest to catching fire. She leads the few early polls. She’s racked up a rangy list of endorsements that somehow spans the downtown-centric Portland Business Alliance, Portland General Electric, and the local Green Party, along with several usually apolitical tech executives like venture capitalist Nitin Khanna and Urban Airship founder Scott Kveton.

To get to this early lead, she spent a lot of money by the standards of Portland politics: over $400,000 at press time. According to campaign staff, her rookie status required expensive new mailing lists and other infrastructure for an “aggressive” push. “She started with about 80 donors and her personal e-mail list,” campaign director Jon Isaacs says. “We needed to introduce her to voters.”

A high burn-rate (to borrow a term from, yes, the entrepreneurial world) may indeed be working for a candidate who wants to jump straight from political obscurity to the city’s executive suite. Brady does seem to be assembling an alliance—big business, small business, green activists—not quite seen before in Portland politics. If she succeeds, the real test begins. The other denizens of City Hall might make her nostalgic for Zenger’s chicken coop. Meanwhile, Portlanders have seen two promising mayors—Tom Potter and Sam Adams—vow transformational leadership, only to limp away after a single term.

To Brady, it’s all about building new coalitions. “Zenger was once one of those cool little ideas that could be big, but it was just a piece of land until we found the right team of supporters,” she says.

“New Seasons succeeded because we pulled together conservative farmers and urbanites who think going to yoga is the same as going to church.”

“It’s all about finding things that unite us.”

“I had never considered running for a city office.”

Generally viewed as the race’s wild card—the upstart who might burn brightly or just flame out—the 38-year-old Smith is a full generation younger than rivals Hales and Brady. Observers tend to credit his palpable smarts—but also warily describe him as “frenetic.” He’s copped to an ADHD diagnosis (now under control, he says) and an “atrocious” driving record. His dog has a Twitter account.

For Smith, the outer east side—which, he points out, would be Oregon’s second largest city—is both a home base and a metaphor for those Portlanders who have not joined Portland’s rise to coveted livability and cultural quirk.

“I realized that if we have another 10 years of underinvestment in neighborhoods that lack political connections, it will be too late to act,” he says. “We’ll lose a chance to create a Portland that works for everyone.”

Smith aims to be the race’s truth-to-power progressive outsider; hence, in part, his choice of David Douglas. “People around here tend to be less avid members of the chattering classes,” he notes. In mid-February, Smith landed the endorsement of an influential pro-cycling and transit group. He’s the candidate most forthrightly critical of the proposed massive (and, some feel, massively flawed) Columbia River Crossing bridge project.

A candidate trying to win the mayoralty by talking up Portland’s least connected neighborhoods will certainly need insurgent strength. Perhaps conveniently, Smith debuted in local politics by founding the Bus Project, a youth-oriented voter turnout initiative that’s become a finishing school for earnest progressives. Whether Smith’s get-out-the-vote expertise (and connections to potential foot soldiers) can shift the relatively small electorate likely to turn out for the city primary remains to be seen. But as he strides the asphalt at David Douglas, Smith seems determined to be a different kind of candidate.

“We need one of the most robust grassroots campaigns in the city’s history.”